Solanone is known as a useful tobacco flavorant and flavor enhancer. It is a mixture consisting primarily of the compounds defined according to the structure: ##STR23## which is indicative of a cis and trans mixture of compounds having the structures: ##STR24##
Isosolanone, an isomer of solanone, is a mixture of cis and trans isomers defined according to the structure: ##STR25## which is indicative of a mixture of cis and trans isomers having the structures: ##STR26##
Isosolanone and solanone are disclosed in a paper by Demole and Berthet entitled "A Chemical Study of Burley Tobacco Flavour (Nicotiana tabacum L.) I. Volatile to medium-volatile constituents", Helvetica Chimica Acta, Volume 55, Fasc. 6(1972) Nr. 175-176, pages 1866-1882, to be present in burley tobacco aroma.
A need has arisen, however, to produce in an economical and efficient manner solanone and isosolanone. The paper by Johnson and Nicholson entitled "The Structure, Chemistry and Synthesis of Solanone, A New Anomalous Terpenoid Ketone from Tobacco" published in J. Org. Chem. 30(9), 2918-21 (1965) discloses a rather complex synthesis for solanone and isosolanone.
Furthermore, in the perfumery art there is a considerable need for constituents having minty, herbal, anisic, cedarleaf, and pennyroyal aroma nuances with floral and coriander-like undertones.
Such fragrance materials have a wide utilization in the presence of the perfumery compound of our invention. A limited amount of such materials that give rise to these properties is available from natural sources but the natural materials are subject to wide variations in quality, are expensive and are often in critically short supply.
In addition, there is a continuing search for food flavor compositions which can vary, fortify, modify, enhance, augment or otherwise improve the flavor and/or aroma of foodstuffs, medicinal products, toothpastes and chewing gums. To be satisfactory, such compositions should be stable, non-toxic and blendable with other ingredients to provide their own unique flavor and aroma nuances without detracting from the coingredients. Preferably such compositions should be naturally occurring or present in natural foodstuffs so that their ingestible safety can be readily recognized. These materials should be capable of being synthesized in a simple and economical manner. The need for safe flavors in the cooked vegetable flavor area and in the garlic area is well known. More specifically, there is a need for development of non-toxic materials which can replace natural materials not readily available having floral, patchouli-like, cooked red beet-like, earthy, garlic and green aroma and taste characteristics.
The instant invention provides the foregoing which the prior art has heretofore failed to provide. Furthermore, nothing in the prior art shows the unexpected, unobvious and advantageous value of the compounds having the structures: ##STR27## wherein Z represents hydrogen, MgX or: ##STR28## and X represents chloro, bromo or iodo or of the compound defined according to the structure: ##STR29## which is indicative of a mixture of cis and trans isomers having the structures: ##STR30##